Jennifer Lopez’s red carpet style is unmatchable. The singer-turned-actress has spent her decades-long career absolutely killing it on the red carpet, but the style icon hasn’t always been as polished as she is in more recent photos. In her very first red carpet appearance, Lopez looks like a totally different woman.
In the over 30 years that Jennifer Lopez has been in the entertainment industry, she’s undergone a massive style transformation. In keeping with changing trends, Lopez typically favors the contoured makeup look made famous by celebrities like the Kardashians.
That hasn’t always been her go-to style look, however. Thanks to the fact that her industry debut was in the late ’90s, the sense of style was vastly different, though there are some similarities. Athleisure was all the rage, just like it is now, but it was expressed in a distinctly 00’s way. While the hip and chic crowd now adore their crop tops and yoga leggings, back then it was all about the tracksuits.
The Start Of Jennifer Lopez’s Iconic Style
One of Lopez’s most iconic style moments came early in her career thanks to the predecessor of the crop top: the belly shirt, as well as her unmistakable pink tracksuit. Though these were the earliest looks that helped set Lopez apart from the crowd early on, neither was her first red carpet look.
How We’ll Always Remember Jenny From The Block
Ever Evolving Sense Of Fashion
It’s fascinating to see the way Jennifer Lopez has evolved her style over the years. She famously got her start as a “Fly Girl” on In Living Color, and her style in the beginning of her career definitely displayed her origins with pride.
Lopez favored sexy, form-fitting frocks with either high hemlines or plunging necklines. The bling, of course, was ever-present in either eye-catching earrings or dazzling bracelets, with the statement necklace being optional.
The Beginning Of JLo’s Red Carpet Domination
In this red carpet photo, dated around spring 1999, Lopez shows that she can rock edgy fashion with ease, as this fashionably ripped silver dress clearly shows. The makeup is what really catches our eye, though. Instead of the carefully sculpted cheekbones and ruthlessly contoured nose, Lopez wears the style of the time: heavy eye makeup, pencil-thin eyebrows, flushed cheeks, and rosy pink lips.
Lopez’s First Red Carpet Looks
It’s stunning how much Lopez’s face has changed, but almost none of it is aging. The different styles of makeup make a world of difference in Lopez’s changing face, but her features are still largely the same. We won’t go so far as to say that Lopez looks younger now than she did in 1999 when she was 30-years-old. But we will say that the new trend in makeup does a much better job of showing off Lopez’s good looks.
This is the very first red carpet appearance we can find of Lopez at the 1999 Grammy Awards. The songstress looked stunning in her glittering, gold tube slip dress. It hugged Lopez’s famed figure, which was already turning heads at the time, like an absolute dream. Her makeup was much more understated than recent red carpet appearances, so much so that we’d almost have trouble recognizing her if we passed her on the street!
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